RU2490265C2 - Пиридазиноновые производные в качестве ингибиторов parp - Google Patents

Пиридазиноновые производные в качестве ингибиторов parp Download PDF

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Publication number: RU2490265C2
Authority: RU; Russia
Prior art keywords: carbonyl; oxo; oxopiperazin; dihydropyridazin; trifluoroacetate
Prior art date: 2007-11-15

Application number

RU2010123874/04A

Other languages

English (en)

Russian (ru)

Other versions

RU2010123874A (ru

Inventor

Данила БРАНКА

Габриэлла ДЕССОЛЕ

Федерика ФЕРРИНЬО

Филип Джоунс

Олаф КИНЦЕЛЬ

Самуэле ЛИЛЛИНИ

Эстер Муралья

Джованна Пескаторе

Карстен Шультц-Фадемрехт

Original Assignee

Институто Ди Ричерке Ди Биолоджиа Молеколаре П. Анджелетти С.П.А.

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2007-11-15

Filing date

2008-11-14

Publication date

2013-08-20

2007-11-15 Priority claimed from GB0722401A external-priority patent/GB0722401D0/en

2008-09-12 Priority claimed from GB0816707A external-priority patent/GB0816707D0/en

2008-11-14 Application filed by Институто Ди Ричерке Ди Биолоджиа Молеколаре П. Анджелетти С.П.А. filed Critical Институто Ди Ричерке Ди Биолоджиа Молеколаре П. Анджелетти С.П.А.

2011-12-20 Publication of RU2010123874A publication Critical patent/RU2010123874A/ru

2013-08-20 Application granted granted Critical

2013-08-20 Publication of RU2490265C2 publication Critical patent/RU2490265C2/ru

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AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims description 10
239000012661 PARP inhibitor Substances 0.000 title description 23
229940121906 Poly ADP ribose polymerase inhibitor Drugs 0.000 title description 23
150000001875 compounds Chemical class 0.000 claims abstract description 308
150000003839 salts Chemical class 0.000 claims abstract description 58
239000003112 inhibitor Substances 0.000 claims abstract description 56
102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 claims abstract description 32
108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 claims abstract description 32
229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 claims abstract description 29
239000003814 drug Substances 0.000 claims abstract description 25
-1 bicyclo [1.1.1] pentyl Chemical group 0.000 claims description 439
125000000217 alkyl group Chemical group 0.000 claims description 141
239000000203 mixture Substances 0.000 claims description 111
229910052736 halogen Inorganic materials 0.000 claims description 93
150000002367 halogens Chemical class 0.000 claims description 91
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 84
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 81
238000000034 method Methods 0.000 claims description 73
238000011282 treatment Methods 0.000 claims description 73
206010028980 Neoplasm Diseases 0.000 claims description 68
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 65
201000011510 cancer Diseases 0.000 claims description 58
229910052760 oxygen Inorganic materials 0.000 claims description 50
229910052717 sulfur Inorganic materials 0.000 claims description 50
125000003545 alkoxy group Chemical group 0.000 claims description 40
229920006395 saturated elastomer Polymers 0.000 claims description 40
125000005842 heteroatom Chemical group 0.000 claims description 39
125000000623 heterocyclic group Chemical group 0.000 claims description 39
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
229910052739 hydrogen Inorganic materials 0.000 claims description 33
239000001257 hydrogen Substances 0.000 claims description 32
125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
230000002265 prevention Effects 0.000 claims description 26
125000003118 aryl group Chemical group 0.000 claims description 25
125000001072 heteroaryl group Chemical group 0.000 claims description 24
125000004093 cyano group Chemical group *C#N 0.000 claims description 23
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 18
150000002431 hydrogen Chemical class 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 15
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 14
125000004429 atom Chemical group 0.000 claims description 13
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 12
208000024172 Cardiovascular disease Diseases 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 9
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
206010012601 diabetes mellitus Diseases 0.000 claims description 9
239000011737 fluorine Substances 0.000 claims description 9
229910052731 fluorine Inorganic materials 0.000 claims description 9
208000027866 inflammatory disease Diseases 0.000 claims description 9
230000000302 ischemic effect Effects 0.000 claims description 9
125000002950 monocyclic group Chemical group 0.000 claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims description 9
ZATJDLMIMGXSOJ-UHFFFAOYSA-N 2,4-dimethylpyridazin-3-one Chemical compound CC1=CC=NN(C)C1=O ZATJDLMIMGXSOJ-UHFFFAOYSA-N 0.000 claims description 8
206010063837 Reperfusion injury Diseases 0.000 claims description 8
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
125000004043 oxo group Chemical group O=* 0.000 claims description 8
230000001976 improved effect Effects 0.000 claims description 7
230000005764 inhibitory process Effects 0.000 claims description 7
230000004770 neurodegeneration Effects 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 6
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
238000011321 prophylaxis Methods 0.000 claims description 6
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 6
208000019553 vascular disease Diseases 0.000 claims description 6
LOVPKEGVBQPBKX-UHFFFAOYSA-N 3-[[3-(3,3-dimethyl-5-oxo-4-phenylpiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(C)(C)N(C=3C=CC=CC=3)C(=O)C2)=N1 LOVPKEGVBQPBKX-UHFFFAOYSA-N 0.000 claims description 5
SGMOVYLUGVDSNT-UHFFFAOYSA-N 3-[[3-(4-cyclopentyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CCCC3)CC2)=N1 SGMOVYLUGVDSNT-UHFFFAOYSA-N 0.000 claims description 5
RWJGRIHHRSKDDD-UHFFFAOYSA-N CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3)C4=CC=CC=C4Cl)C Chemical compound CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3)C4=CC=CC=C4Cl)C RWJGRIHHRSKDDD-UHFFFAOYSA-N 0.000 claims description 5
206010038997 Retroviral infections Diseases 0.000 claims description 5
QFLXYLHMJUPUTA-UHFFFAOYSA-N [3-[[3-(4-cyclohexyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-6-oxo-1,5-dihydropyridazin-2-yl] 2,2,2-trifluoroacetate Chemical compound FC(C(=O)ON1NC(C(C(=C1CC1=CC(=C(C=C1)F)C(=O)N1CC(N(CC1)C1CCCCC1)=O)C)C)=O)(F)F QFLXYLHMJUPUTA-UHFFFAOYSA-N 0.000 claims description 5
AGZWIOIOHSYOBQ-UHFFFAOYSA-N [3-[[3-(4-cyclopentyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-6-oxo-5-(trifluoromethyl)-1,5-dihydropyridazin-2-yl] 2,2,2-trifluoroacetate Chemical compound FC(C(=O)ON1NC(C(C=C1CC1=CC(=C(C=C1)F)C(=O)N1CC(N(CC1)C1CCCC1)=O)C(F)(F)F)=O)(F)F AGZWIOIOHSYOBQ-UHFFFAOYSA-N 0.000 claims description 5
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
125000002883 imidazolyl group Chemical group 0.000 claims description 5
208000015181 infectious disease Diseases 0.000 claims description 5
208000015122 neurodegenerative disease Diseases 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
125000003003 spiro group Chemical group 0.000 claims description 5
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
125000000335 thiazolyl group Chemical group 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
CUVGGFVJAPAUTR-UHFFFAOYSA-N CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3C)C4CCCCC4)C Chemical compound CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3C)C4CCCCC4)C CUVGGFVJAPAUTR-UHFFFAOYSA-N 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
208000001647 Renal Insufficiency Diseases 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000005972 dihydrochromenyl group Chemical group 0.000 claims description 4
201000006370 kidney failure Diseases 0.000 claims description 4
125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
MMYQUKVDUAHGLE-UHFFFAOYSA-N 3-[[4-fluoro-3-(3-oxo-4-pyridin-3-ylpiperazine-1-carbonyl)phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC2)C=2C=NC=CC=2)=N1 MMYQUKVDUAHGLE-UHFFFAOYSA-N 0.000 claims description 3
NPRRPYUSGSZKOW-UHFFFAOYSA-N 3-[[4-fluoro-3-(3-oxo-4-quinolin-3-ylpiperazine-1-carbonyl)phenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC2)C=2C=C3C=CC=CC3=NC=2)=N1 NPRRPYUSGSZKOW-UHFFFAOYSA-N 0.000 claims description 3
WVLVNXURIODZRA-UHFFFAOYSA-N C1CCC(CC1)N2CCN(CC2=O)C(=O)C3=C(C=CC(=C3)CC4=CC(C(=O)NN4OC(=O)C(F)(F)F)C(F)(F)F)F Chemical compound C1CCC(CC1)N2CCN(CC2=O)C(=O)C3=C(C=CC(=C3)CC4=CC(C(=O)NN4OC(=O)C(F)(F)F)C(F)(F)F)F WVLVNXURIODZRA-UHFFFAOYSA-N 0.000 claims description 3
RBHNOTMIJPRQBC-UHFFFAOYSA-N CC(C(C)=C(CC(C=C1)=CC(C(N(CCN2C3CC4=CC=CC=C4CC3)CC2=O)=O)=C1F)N(N1)OC(C(F)(F)F)=O)C1=O Chemical compound CC(C(C)=C(CC(C=C1)=CC(C(N(CCN2C3CC4=CC=CC=C4CC3)CC2=O)=O)=C1F)N(N1)OC(C(F)(F)F)=O)C1=O RBHNOTMIJPRQBC-UHFFFAOYSA-N 0.000 claims description 3
LRWDEVQNGZXACC-UHFFFAOYSA-N CC(C(C)=C(CC(C=C1)=CC(C(N(CCN2CC3C4=CC=CC=C4CCC3)CC2=O)=O)=C1F)N(N1)OC(C(F)(F)F)=O)C1=O Chemical compound CC(C(C)=C(CC(C=C1)=CC(C(N(CCN2CC3C4=CC=CC=C4CCC3)CC2=O)=O)=C1F)N(N1)OC(C(F)(F)F)=O)C1=O LRWDEVQNGZXACC-UHFFFAOYSA-N 0.000 claims description 3
DRNHVHQEQKZMAL-UHFFFAOYSA-N CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3)C4=CC=C(C=C4)Cl)C Chemical compound CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3)C4=CC=C(C=C4)Cl)C DRNHVHQEQKZMAL-UHFFFAOYSA-N 0.000 claims description 3
NWYXCXIBUKOTMG-UHFFFAOYSA-N CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3)C4=CC=CC=C4)C Chemical compound CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3)C4=CC=CC=C4)C NWYXCXIBUKOTMG-UHFFFAOYSA-N 0.000 claims description 3
RSTCDRZGOWNHOF-UHFFFAOYSA-N CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3)CC(C)C(F)(F)F)C Chemical compound CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3)CC(C)C(F)(F)F)C RSTCDRZGOWNHOF-UHFFFAOYSA-N 0.000 claims description 3
NYNOMUZWNYLQOO-UHFFFAOYSA-N CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3)CC4(CCOCC4)C5=CC=CC=C5)C Chemical compound CC1C(=C(N(NC1=O)OC(=O)C(F)(F)F)CC2=CC(=C(C=C2)F)C(=O)N3CCN(C(=O)C3)CC4(CCOCC4)C5=CC=CC=C5)C NYNOMUZWNYLQOO-UHFFFAOYSA-N 0.000 claims description 3
NHPHCISMLQIKKW-UHFFFAOYSA-N [3-[[3-(4-cyclobutyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-6-oxo-1,5-dihydropyridazin-2-yl] 2,2,2-trifluoroacetate Chemical compound FC(C(=O)ON1NC(C(C(=C1CC1=CC(=C(C=C1)F)C(=O)N1CC(N(CC1)C1CCC1)=O)C)C)=O)(F)F NHPHCISMLQIKKW-UHFFFAOYSA-N 0.000 claims description 3
OUCZTXRPMSCINW-UHFFFAOYSA-N [3-[[3-(4-cyclohexyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4-ethyl-5-methyl-6-oxopyridazin-1-yl] 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)ON1C(=O)C(C)=C(CC)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CCCCC3)CC2)=N1 OUCZTXRPMSCINW-UHFFFAOYSA-N 0.000 claims description 3
CIIXQFGFWXRNRU-UHFFFAOYSA-N [3-[[3-(4-cyclohexyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4-methyl-6-oxo-5-(trifluoromethyl)pyridazin-1-yl] 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)ON1C(=O)C(C(F)(F)F)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CCCCC3)CC2)=N1 CIIXQFGFWXRNRU-UHFFFAOYSA-N 0.000 claims description 3
IQLJBFUYXUQJAH-UHFFFAOYSA-N [3-[[4-fluoro-3-(4-thiophen-3-ylpiperazine-1-carbonyl)phenyl]methyl]-4,5-dimethyl-6-oxopyridazin-1-yl] 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)ON1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CCN(CC2)C2=CSC=C2)=N1 IQLJBFUYXUQJAH-UHFFFAOYSA-N 0.000 claims description 3
IVDNZCSSHYLESM-UHFFFAOYSA-N [3-[[4-fluoro-3-[3-oxo-4-[4-(trifluoromethyl)pyridin-2-yl]piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-6-oxopyridazin-1-yl] 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)ON1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC2)C=2N=CC=C(C=2)C(F)(F)F)=N1 IVDNZCSSHYLESM-UHFFFAOYSA-N 0.000 claims description 3
NRFNBNAZXMMBCV-UHFFFAOYSA-N [3-[[4-fluoro-3-[3-oxo-4-[5-(trifluoromethyl)pyridin-3-yl]piperazine-1-carbonyl]phenyl]methyl]-4,5-dimethyl-6-oxopyridazin-1-yl] 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)ON1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(CC2)C=2C=C(C=NC=2)C(F)(F)F)=N1 NRFNBNAZXMMBCV-UHFFFAOYSA-N 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
230000002207 retinal effect Effects 0.000 claims description 3
VJTRXXZCGWHXKE-MRXNPFEDSA-N (9ar)-2-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-3-yl)methyl]-2-fluorobenzoyl]-3,6,7,8,9,9a-hexahydro-1h-pyrido[1,2-a]pyrazin-4-one Chemical compound N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N3CCCC[C@@H]3C2)=N1 VJTRXXZCGWHXKE-MRXNPFEDSA-N 0.000 claims description 2
VJTRXXZCGWHXKE-INIZCTEOSA-N (9as)-2-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-3-yl)methyl]-2-fluorobenzoyl]-3,6,7,8,9,9a-hexahydro-1h-pyrido[1,2-a]pyrazin-4-one Chemical compound N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N3CCCC[C@H]3C2)=N1 VJTRXXZCGWHXKE-INIZCTEOSA-N 0.000 claims description 2
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
HYCAGUHRBSKSLG-UHFFFAOYSA-N 1-cyclopropyl-4-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-3-yl)methyl]-2-fluorobenzoyl]-1,4-diazepan-2-one Chemical compound N1C(=O)C(C)=C(C)C(CC=2C=C(C(F)=CC=2)C(=O)N2CC(=O)N(C3CC3)CCC2)=N1 HYCAGUHRBSKSLG-UHFFFAOYSA-N 0.000 claims description 2
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
OFRDHELOEGITNL-CQSZACIVSA-N 3-[(2r)-4-[5-[(4,5-dimethyl-6-oxo-1h-pyridazin-3-yl)methyl]-2-fluorobenzoyl]-2-methyl-6-oxopiperazin-1-yl]-5-fluorobenzonitrile Chemical compound C([C@H]1C)N(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1=CC(F)=CC(C#N)=C1 OFRDHELOEGITNL-CQSZACIVSA-N 0.000 claims description 2
KUAYOHCIBZUBSQ-UHFFFAOYSA-N 3-[[2-bromo-5-(4-cyclopentyl-3-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound CC1=C(C)C(=O)NN=C1CC1=CC(C(=O)N2CC(=O)N(C3CCCC3)CC2)=C(F)C=C1Br KUAYOHCIBZUBSQ-UHFFFAOYSA-N 0.000 claims description 2
HKCNWPZOGXXWCQ-UHFFFAOYSA-N 3-[[3-(4-cyclobutyl-3-ethyl-5-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound CCC1CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1CCC1 HKCNWPZOGXXWCQ-UHFFFAOYSA-N 0.000 claims description 2
QPMCMWZABOOUSH-UHFFFAOYSA-N 3-[[3-(4-cyclobutyl-3-methyl-5-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound CC1CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1CCC1 QPMCMWZABOOUSH-UHFFFAOYSA-N 0.000 claims description 2
HZEUKGTVBAQKDU-UHFFFAOYSA-N 3-[[3-(4-cyclohexyl-3-ethyl-5-oxopiperazine-1-carbonyl)-4-fluorophenyl]methyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound CCC1CN(C(=O)C=2C(=CC=C(CC=3C(=C(C)C(=O)NN=3)C)C=2)F)CC(=O)N1C1CCCCC1 HZEUKGTVBAQKDU-UHFFFAOYSA-N 0.000 claims description 2
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AKIGDHHFVMHBQD-CYBMUJFWSA-N 3-[[3-[(3r)-4-cyclopentyl-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-5-(trifluoromethyl)-1h-pyridazin-6-one Chemical compound C([C@H]1C)N(C(=O)C=2C(=CC=C(CC3=NNC(=O)C(=C3)C(F)(F)F)C=2)F)CC(=O)N1C1CCCC1 AKIGDHHFVMHBQD-CYBMUJFWSA-N 0.000 claims description 2
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AKIGDHHFVMHBQD-ZDUSSCGKSA-N 3-[[3-[(3s)-4-cyclopentyl-3-methyl-5-oxopiperazine-1-carbonyl]-4-fluorophenyl]methyl]-5-(trifluoromethyl)-1h-pyridazin-6-one Chemical compound C([C@@H]1C)N(C(=O)C=2C(=CC=C(CC3=NNC(=O)C(=C3)C(F)(F)F)C=2)F)CC(=O)N1C1CCCC1 AKIGDHHFVMHBQD-ZDUSSCGKSA-N 0.000 claims description 2
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Classifications

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- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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RU2010123874/04A 2007-11-15 2008-11-14 Пиридазиноновые производные в качестве ингибиторов parp RU2490265C2 (ru)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
GB0722401.7		2007-11-15
GB0722401A GB0722401D0 (en)	2007-11-15	2007-11-15	Therapeutic compounds
GB0816707A GB0816707D0 (en)	2008-09-12	2008-09-12	Therapeutic compounds
GB0816707.4		2008-09-12
PCT/GB2008/051063 WO2009063244A1 (fr)	2007-11-15	2008-11-14	Derivés de pyridazinone inhibiteurs de la parp

Publications (2)

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RU2010123874A RU2010123874A (ru)	2011-12-20
RU2490265C2 true RU2490265C2 (ru)	2013-08-20

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US (1)	US8268827B2 (fr)
EP (1)	EP2220073B1 (fr)
JP (1)	JP5758630B2 (fr)
KR (1)	KR101641596B1 (fr)
CN (1)	CN101855221B (fr)
AU (1)	AU2008322676B9 (fr)
CA (1)	CA2704714C (fr)
ES (1)	ES2524787T3 (fr)
IL (1)	IL205142A (fr)
MX (1)	MX2010005070A (fr)
NZ (1)	NZ585395A (fr)
RU (1)	RU2490265C2 (fr)
WO (1)	WO2009063244A1 (fr)
ZA (1)	ZA201002466B (fr)

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- 2008-11-14 MX MX2010005070A patent/MX2010005070A/es active IP Right Grant
- 2008-11-14 AU AU2008322676A patent/AU2008322676B9/en active Active
- 2008-11-14 US US12/739,262 patent/US8268827B2/en active Active
- 2008-11-14 ES ES08850429.5T patent/ES2524787T3/es active Active
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- 2008-11-14 JP JP2010533666A patent/JP5758630B2/ja active Active
- 2008-11-14 NZ NZ585395A patent/NZ585395A/en unknown
- 2008-11-14 CN CN2008801155905A patent/CN101855221B/zh active Active
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KR20100087220A (ko)	2010-08-03
AU2008322676B2 (en)	2013-12-05
RU2010123874A (ru)	2011-12-20
MX2010005070A (es)	2010-05-24
IL205142A0 (en)	2010-11-30
BRPI0820236A2 (pt)	2015-06-16
IL205142A (en)	2014-09-30
CN101855221A (zh)	2010-10-06
EP2220073B1 (fr)	2014-09-03
AU2008322676A1 (en)	2009-05-22
ES2524787T3 (es)	2014-12-12
CA2704714C (fr)	2018-12-04
ZA201002466B (en)	2010-12-29
AU2008322676B9 (en)	2014-03-27
CA2704714A1 (fr)	2009-05-22
US20100261709A1 (en)	2010-10-14
KR101641596B1 (ko)	2016-07-21
JP2011503166A (ja)	2011-01-27
US8268827B2 (en)	2012-09-18
CN101855221B (zh)	2013-10-30
NZ585395A (en)	2012-03-30
JP5758630B2 (ja)	2015-08-05
WO2009063244A1 (fr)	2009-05-22
EP2220073A1 (fr)	2010-08-25

Publication	Publication Date	Title
RU2490265C2 (ru)	2013-08-20	Пиридазиноновые производные в качестве ингибиторов parp
AU2008204380B2 (en)	2013-08-15	Amide substituted indazoles as poly(ADP-ribose)polymerase (PARP) inhibitors
US8436185B2 (en)	2013-05-07	Pharmaceutically acceptable salts of 2-{4-[(3S)-piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide
US8354413B2 (en)	2013-01-15	Quinolin-4-one and 4-oxodihydrocinnoline derivatives as inhibitors of poly(ADP-ribose) polymerase (PARP)
NZ578256A (en)	2011-12-22	Amide substituted indazoles as poly(adp-ribose)polymerase (parp) inhibitors
BRPI0820236B1 (pt)	2025-05-27	Compostos derivados de piridazinona, composição farmacêutica compreendendo os mesmos e usos dos referidos compostos
HK40006670A (en)	2020-05-22	Amide substituted indazoles as poly(adp-ribose)polymerase (parp) inhibitors
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2014-08-27	PC41	Official registration of the transfer of exclusive right	Effective date: 20140807

RU2490265C2 - Пиридазиноновые производные в качестве ингибиторов parp - Google Patents

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